Extending pummerer reaction chemistry. Application to the total synthesis of (+/-)-dibromoagelaspongin.
The sponge metabolite dibromoagelaspongin was synthesized in 16 steps from imidazole. The route features two successive oxidative cyclizations with complete control of regiochemistry to deliver the unusual triaminomethane core of the target. These oxidative cyclizations likely resulted from Pummerer-like processes on the imidazole-2-sulfoxide (sulfide) precursors.
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
Fodor
Matthew D
MD
D000470:Alkaloids / Q000138:chemical synthesis; D003500:Cyclization; D006146:Guanidines / Q000138:chemical synthesis; D007093:Imidazoles / Q000737:chemistry; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry; D013454:Sulfoxides / Q000737:chemistry
D000470:Alkaloids; D006146:Guanidines; D007093:Imidazoles; D011758:Pyrroles; D013440:Sulfides; D013454:Sulfoxides; C519749:dibromoagelaspongin methyl ether